반응 #11465

반응 방정식

Isobutyryl chloride

1-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride

material

1-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine

triethylamine

→

N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide

수율 74.5%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타The solvents were removed under reduced pressure
2. 2
   기타The residue was partitioned between chloroform (250 mL) and water (250 mL)
3. 3
   workup.ADDITIONcontaining 10 g of sodium carbonate (pH 12)
4. 4
   추출extracted with chloroform for 24 hours
5. 5
   건조The extract was dried over magnesium sulfate
6. 6
   농축concentrated under reduced pressure
7. 7
   기타to provide a light yellow oil
8. 8
   기타The oil was purified by chromatography (silica gel eluting with 85/15 dichloromethane/methanol)

실험 절차

Isobutyryl chloride (1.3 mL, 12.2 mmol) was added dropwise to a mixture of 1-(2-aminoethyl)-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-4-amine hydrochloride (4.0 g of material from Example 24, 12.2 mmol), triethylamine (85 mL, 610 mmol) and dichloromethane (400 mL). After 15 minutes analysis by high performance liquid chromatography indicated that the reaction was complete. The solvents were removed under reduced pressure. The residue was partitioned between chloroform (250 mL) and water (250 mL) containing 10 g of sodium carbonate (pH 12). This mixture was placed in a continuous extractor and extracted with chloroform for 24 hours. The extract was dried over magnesium sulfate and then concentrated under reduced pressure to provide a light yellow oil. The oil was purified by chromatography (silica gel eluting with 85/15 dichloromethane/methanol) to provide 2.63 g of N-[2-(4-amino-2,6,7-trimethyl-1H-imidazo[4,5-c]pyridin-1-yl)ethyl]-2-methylpropanamide as a white powder, m.p. 220–222° C.

출처